(Q89289670)

English

3-Fluoro-4-hydroxyprolines: Synthesis, Conformational Analysis, and Stereoselective Recognition by the VHL E3 Ubiquitin Ligase for Targeted Protein Degradation

scientific article published on 12 July 2018

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Europe PubMed Central

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https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:29949369%20AND%20SRC:MED&resulttype=core&format=json

2 April 2020

3-Fluoro-4-hydroxyprolines: Synthesis, Conformational Analysis, and Stereoselective Recognition by the VHL E3 Ubiquitin Ligase for Targeted Protein Degradation (English)

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PMC publication ID

https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:29949369%20AND%20SRC:MED&resulttype=core&format=json

2 April 2020

stereoselectivity

1 reference

based on heuristic

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corrigendum / erratum

Correction to "3-Fluoro-4-hydroxyprolines: Synthesis, Conformational Analysis, and Stereoselective Recognition by the VHL E3 Ubiquitin Ligase for Targeted Protein Degradation"

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2 April 2020

2

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2 April 2020

Andrew C Runcie

6

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2 April 2020

7

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2 April 2020

11

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2 April 2020

author name string

Guilherme V Castro

3

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2 April 2020

Kwok-Ho Chan

4

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2 April 2020

Jane E Wright

5

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2 April 2020

William T A Harrison

8

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2 April 2020

Eun-Jung Ko

9

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2 April 2020

Daniel Fletcher

10

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2 April 2020

language of work or name

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Journal of the American Chemical Society

publication date

12 July 2018

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2 April 2020

number of pages

15

1 reference

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inferred from page(s)

Journal of the American Chemical Society

1 reference

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2 April 2020

140

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2 April 2020

29

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Europe PubMed Central

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2 April 2020

9299-9313

1 reference

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2 April 2020

Structure of the VHL-ElonginC-ElonginB complex: implications for VHL tumor suppressor function

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Rbx1, a component of the VHL tumor suppressor complex and SCF ubiquitin ligase

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

The tumour suppressor protein VHL targets hypoxia-inducible factors for oxygen-dependent proteolysis

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Conformational stability of collagen relies on a stereoelectronic effect

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Short, highly efficient syntheses of protected 3-azido- and 4-azidoproline and their precursors

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Stereoselective Reactions ofN-(9-Phenylfluoren-9-yl)-4-oxoproline Enolates. An Expedient Route for the Preparation of Conformationally Restricted Amino Acid Analogues

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Collagen stability: insights from NMR spectroscopic and hybrid density functional computational investigations of the effect of electronegative substituents on prolyl ring conformations

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Structure of an HIF-1alpha -pVHL complex: hydroxyproline recognition in signaling

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Structural basis for the recognition of hydroxyproline in HIF-1 alpha by pVHL

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Effect of 3-hydroxyproline residues on collagen stability

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Oxygen sensing by HIF hydroxylases

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

The impact of pyrrolidine hydroxylation on the conformation of proline-containing peptides

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Different effects of 4-hydroxyproline and 4-fluoroproline on the stability of collagen triple helix

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Protein posttranslational modifications: the chemistry of proteome diversifications

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Stereoelectronic and steric effects in the collagen triple helix: toward a code for strand association

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Discovery of potent, selective 4-fluoroproline-based thrombin inhibitors with improved metabolic stability

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Fluoroproline Flip-Flop: Regiochemical Reversal of a Stereoelectronic Effect on Peptide and Protein Structures

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Fluorine in medicinal chemistry

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Synthetic Biology of Proteins: Tuning GFPs Folding and Stability with Fluoroproline

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Evidence for a stereoelectronic effect in human oxygen sensing.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Hydrogen bonding, electrostatic potential, and molecular design.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Synthesis of a carboxylate functionalized bis-amino acid monomer.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

3S-fluoroproline as a probe to monitor proline isomerization during protein folding by 19F-NMR.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Prolyl 4-hydroxylase

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Revealing noncovalent interactions

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

The aberrance of the 4S diastereomer of 4-hydroxyproline

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

The hypoxia-inducible transcription factor pathway regulates oxygen sensing in the simplest animal, Trichoplax adhaerens

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Use of cis-[18F]fluoro-proline for assessment of exercise-related collagen synthesis in musculoskeletal connective tissue

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

3-fluoro-GABA enantiomers: exploring the conformation of GABA binding to GABAA receptors and GABA aminotransferase

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Rational design of protein stability: effect of (2S,4R)-4-fluoroproline on the stability and folding pathway of ubiquitin

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Targeting the von Hippel–Lindau E3 Ubiquitin Ligase Using Small Molecules To Disrupt the VHL/HIF-1α Interaction

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

An unexpected and significantly lower hydrogen-bond-donating capacity of fluorohydrins compared to nonfluorinated alcohols.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

3-Fluoro-N-methyl-D-aspartic acid (3F-NMDA) Stereoisomers as Conformational Probes for Exploring Agonist Binding at NMDA Receptors

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Dissecting Fragment-Based Lead Discovery at the von Hippel-Lindau Protein:Hypoxia Inducible Factor 1α Protein-Protein Interface

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Proline editing: a general and practical approach to the synthesis of functionally and structurally diverse peptides. Analysis of steric versus stereoelectronic effects of 4-substituted prolines on conformation within peptides

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Intramolecular OH···FC hydrogen bonding in fluorinated carbohydrates: CHF is a better hydrogen bond acceptor than CF2

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Small-molecule control of intracellular protein levels through modulation of the ubiquitin proteasome system

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Extended Structure–Activity Relationship and Pharmacokinetic Investigation of (4-Quinolinoyl)glycyl-2-cyanopyrrolidine Inhibitors of Fibroblast Activation Protein (FAP)

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Structure-Guided Design and Optimization of Small Molecules Targeting the Protein–Protein Interaction between the von Hippel–Lindau (VHL) E3 Ubiquitin Ligase and the Hypoxia Inducible Factor (HIF) Alpha Subunit with in Vitro Nanomolar Affinities

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Synthesis and biological evaluation of (-)-kainic acid analogues as phospholipase D-coupled metabotropic glutamate receptor ligands

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

γ-(S)-Trifluoromethyl proline: evaluation as a structural substitute of proline for solid state (19)F-NMR peptide studies.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Selective Small Molecule Induced Degradation of the BET Bromodomain Protein BRD4.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Catalytic in vivo protein knockdown by small-molecule PROTACs.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Influence of Fluorination on the Conformational Properties and Hydrogen-Bond Acidity of Benzyl Alcohol Derivatives.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Applications of Fluorine in Medicinal Chemistry

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Modular PROTAC Design for the Degradation of Oncogenic BCR-ABL.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Small-Molecule PROTACS: New Approaches to Protein Degradation

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Targeted Protein Degradation by Small Molecules

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Potent and selective chemical probe of hypoxic signalling downstream of HIF-α hydroxylation via VHL inhibition

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Structural basis of PROTAC cooperative recognition for selective protein degradation

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Impact of Target Warhead and Linkage Vector on Inducing Protein Degradation: Comparison of Bromodomain and Extra-Terminal (BET) Degraders Derived from Triazolodiazepine (JQ1) and Tetrahydroquinoline (I-BET726) BET Inhibitor Scaffolds

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Identification and Characterization of Von Hippel-Lindau-Recruiting Proteolysis Targeting Chimeras (PROTACs) of TANK-Binding Kinase 1.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

The n→π* Interaction

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Group-Based Optimization of Potent and Cell-Active Inhibitors of the von Hippel-Lindau (VHL) E3 Ubiquitin Ligase: Structure-Activity Relationships Leading to the Chemical Probe (2S,4R)-1-((S)-2-(1-Cyanocyclopropanecarboxamido)-3,3-dimethylbutanoyl)-

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Homo-PROTACs: bivalent small-molecule dimerizers of the VHL E3 ubiquitin ligase to induce self-degradation.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Molecular recognition of ternary complexes: a new dimension in the structure-guided design of chemical degraders

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

The Use of Fluoroproline in MUC1 Antigen Enables Efficient Detection of Antibodies in Patients with Prostate Cancer.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

2017 FDA drug approvals

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Functional TRIM24 degrader via conjugation of ineffectual bromodomain and VHL ligands.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

The dTAG system for immediate and target-specific protein degradation.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Thioamide substitution to probe the hydroxyproline recognition of VHL ligands.

1 reference

https://pubmed.ncbi.nlm.nih.gov/29949369

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Identifiers

10.1021/JACS.8B05807

1 reference

Europe PubMed Central

PMC publication ID

https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:29949369%20AND%20SRC:MED&resulttype=core&format=json

2 April 2020

PMC publication ID

1 reference

Europe PubMed Central

PMC publication ID

https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:29949369%20AND%20SRC:MED&resulttype=core&format=json

2 April 2020

PubMed publication ID

1 reference

Europe PubMed Central

PMC publication ID

https://www.ebi.ac.uk/europepmc/webservices/rest/search?query=EXT_ID:29949369%20AND%20SRC:MED&resulttype=core&format=json

2 April 2020

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